


There's Nothing Left to Lose

by FolleseGaskarth



Category: Free!
Genre: Crossdressing, Dirty Talk, M/M, PWP, Porn, Porn Without Plot
Language: English
Status: Completed
Published: 2014-10-20
Updated: 2014-10-20
Packaged: 2018-02-21 23:28:30
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,508
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2486174
Author URL: https://archiveofourown.org/users/FolleseGaskarth/pseuds/FolleseGaskarth
Summary: <blockquote class="userstuff">
              <p>Nitori has this small collection of feminine clothes he hadn't worn in public... until today.</p>
            </blockquote>





	There's Nothing Left to Lose

**Author's Note:**

> I haven't posted something in so long and I'm so sorry. I've been really busy with a lot of things and I hope to have more work up soon ^-^ This is my first work for the Free! fandom and I hope you guys like it <3

He didn’t wear it often. It was just a simple black skirt hidden in the back of his closet. Okay, so he had a few dresses and thigh-highs. And maybe some lingerie and garter belts, but he was focused on the skirt. They finally had a dress-down day and he had no idea what to wear. He reached his hand into the closet, touching the material of the skirt as if testing it. He pulled it out, examining it more closely. He liked it; he liked it a lot. But he hadn’t ever worn it in public. 

“No time like the present.” He thinks and quickly finds a top to go with it. 

He was glad his Senpai wasn’t in the room. He’d left earlier to go for a run before classes and probably wouldn’t come back. He slipped on the simple, pleated, black skirt and smiled, ravishing in the way it felt against his thighs and boy-shorts. (He may have never worn feminine clothes in public but he surely loved feminine underwear. He still remembers that time he went to class with a thong and spent the whole day trying to suppress his urges with every brush against Matsuoka-Senpai.) He paired the skirt with a simple black t-shirt. It still needed something more though. He decided to go the extra mile and slipped on some black thigh-highs. Some sheer, little things that he was completely enamored with. To top it off, he thought his short, black, biker boots would work. 

He stared at himself in the mirror, smiling from how much he loved his outfit. He wondered why he hadn’t done it before; it made him so happy. He blushed a bit, frowning as he thought what would happen if other people didn’t like it and teased him. He just hoped he was in a safe enough environment. Besides, he had a pretty good relationship with Matsuoka-Senpai. He was sure to defend him. He took one final breath before tossing his bag over his shoulder and heading out. He froze up right away, coming eye-to-eye with Mikoshiba-Senpai. He held his breath as he was eyed up and down. He felt his heart drop as Mikoshiba-Senpai smiled, thinking he was gonna laugh at him but instead he just chuckled and spoke,

“Y’know, it actually looks pretty good on you, Nitori.” He blushed and smiled.  
“Thank you.” He mustered back in a small voice before Mikoshiba-Senpai walked off. 

He exhaled again, thinking that now he had one guaranteed person who would defend him. He continued on to class, his skirt almost swishing with every little swivel of his hips. He noticed a few people giving him looks but he didn’t pay much attention to them, seeing as they didn’t bother him. He didn’t blame them either; it wasn’t every day you saw a skirt on a boy. Their looks only seemed to give him more confidence: he kind of liked the attention. He strided into homeroom, taking his rightful seat and smirking as the teacher and a few students alike fell silent and stared at him. He shrugged slightly and so did they, returning to their conversations. Matsuoka-Senpai walked in a few minutes later, taking his seat next to Nitori but he didn’t seem to notice his outfit. Matsuoka-Senapi wasn’t the type to look at people too much; he’d just glance at your face and continue speaking. If he did have a look at Nitori’s outfit, it would’ve been a small glance which, with all-black clothes and the skirt going slightly over the thigh-highs, made it appear as if Nitori was wearing pants. 

“Yo.” Matsuoka-Senpai said as he sat down.  
“Morning.” Nitori replied in his bright, somewhat shy voice. 

Just as expected, he didn’t notice Nitori’s outfit but Nitori wasn’t complaining. He knew he’d have another opportunity to show his senpai his skirt. He didn’t know why he was so excited to do so but he assumed it had something to do with the fact that he wanted to see his senpai flustered. And he was certainly not disappointed. He stood a little bit before his senpai as they were headed to class and he was certainly noticed then. He noticed Matsuoka-Senpai’s eyes go wide, his cheeks go red as Nitori calmly asked,

“Ready to go?” He didn’t answer, just stared and allowed his jaw to go slack. “Senpai?” Nitori asked again, smiling like the little shit he was when Matsuoka-Senpai didn’t answer. 

Matsuoka-Senpai stood up, walking away with his hand over his mouth and soon smoothing over his face. Nitori thought he was being ignored and frowned until he noticed that Matsuoka-Senpai had slowed down, turning his head and motioning his hand for Nitori to walk with him. He still said nothing as they got to class and he was not spoken to until lunchtime. He had asked for a pencil and received one wordlessly. He inquired on Matsuoka-Senpai’s grade on the returned Math quiz and just got a thumbs-up. He smiled all along the day, knowing that his senpai was just flustered, and that was exactly what he wanted. When they finally got to lunch, Matsuoka-Senpai was the first to speak as they sat on the grass somewhere a little further away from everyone. 

“Why do you even own that?” Nitori’s head whipped up quickly from his bento at the sound of Matsuoka-Senpai’s voice. He smiled innocently; he knew exactly what Matsuoka-Senpai was referring to.  
“I like girly clothes, Matsuoka-Senpai.”  
“Stop calling me that. I told you, it’s Rin,” He quickly spit back harmlessly before continuing. “Besides, why did you chose today? Why not before today?” He blushed and smiled even harder, knowing that Mat-- Rin-Senpai had wanted to see this sight much earlier than just today.  
“I’ve always been shy about it, Rin-Senpai,” Things got quiet as Rin-Senpai picked at his food. “Do you not like it?” Nitori teased, wanting to have a complete reaction. He noticed Rin-Senpai go bright red, almost as deep as his hair as he kept his head down.  
“It’s nice.” He murmured before shoving some rice in his mouth.  
“Really?” Nitori pressed on, leaning forward a bit.  
“Yeah.” Rin-Senpai almost growled back, barely meeting Nitori’s eyes. Nitori smiled to himself and sat back down Indian-style. Rin-Senpai noticed the silence and absence of a shadow over him so he assumed it was safe to look up and was quickly met with the view of Nitori’s dark-gray, really tight underwear.  
“Nitori!” He quickly exclaimed. Nitori jumped, yelping.  
“W-What, Rin-Senpai?!”  
“Don’t… Don’t sit like that.” He spoke softly, avoiding his gaze from the lewd sight.  
“Ohh…” Nitori blushed, repositioning himself to drag his legs to the side. “Sorry, Rin-Senpai. I forget.” They stayed quiet for a few seconds, Rin-Senpai’s response being,  
“So you wear girly underwear too?” He must’ve noticed the slight lace and bows along the boy-shorts. Nitori didn’t think he could turn any darker, but that certainly didn’t mean he wasn’t enjoying this. He nodded.  
“It feels nicer than boys’ underwear.”  
“R-Really?” It was the first time he ever heard Rin-Senpai stutter and he took a large amount of pride in the noise. “How?” Nitori batted his eyelashes and picked at his food.  
“I like it when it’s tight.” Rin-Senpai nearly choked on his food, thinking of something else entirely. 

~~~~~

The day went on and Rin really wished he’d kept his mouth shut because the conversation only worked to make him more excited. He couldn’t stop thinking about how cute Nitori’s underwear was and he imagined it’d only be better if he could see a wet spot forming on them. 

“Fuck,” Rin thought. “Dead puppies, dead puppies, just think of dead puppies.” He told himself as he tried to get through his last few classes. 

It became worse however when he remembered that Nitori shared a room with him. He had to walk back with him. He had to live with him. And he didn’t know how much longer he was planning on wearing that skirt. Well, he wasn’t going to be wearing anything for much longer if Rin had a say in it. 

“Dead fucking puppies.” He thought to himself again and Nitori pressed against his side innocently to get him to move along now that the school day was done.

“I’m going for a run.” He announced the second they got into the dorm. Luckily there was no practice today, lest Nitori break out a two-piece or some skimpy little Speedo.  
“But you went on a run this morning, Rin-Senpai.” He paused, realizing he had but then realizing he didn’t need to justify his actions.  
“And I can go for another. A little exercise never killed anyone, Ai.” And with that he was out the door.

He ran for about an hour, picking up dinner for himself and Nitori afterwards. The sun was setting by the time he got back to their dorm. 

“I’m home, Ai-” His last syllable was cut off as he noticed Nitori on the top bunk, a pencil between his teeth and a notebook on his lap as he was lost in thought, finishing up homework. This was a normal sight for Rin but what really broke him was the fact that he still had that stupid skirt on, his legs open and showcasing his girly underwear. Rin swore he could see the bump in them.  
“Oh,” Nitori quickly closed his legs, blushing as he noticed Rin-Senpai’s eyes between them. “Sorry, Rin-Senpai. Welcome back.” Rin grumbled a bit.  
“I brought dinner.” He spoke avoiding Nitori’s eyes again.  
“Thank you,” Nitori smiled and made his way off of his bed to grab the container with his food, giving his senpai a little side hug which Rin tensed up at. “You didn’t have to; I would’ve just gone to the cafeteria.”  
“I-It’s fine,” Rin stuttered again and knew that Nitori had noticed again but he decided to ignore it. “I was already getting some for myself so I figured why not.” This wasn’t much of a surprise to either of them; Rin often brought back dinner for Nitori when he bought dinner for himself. 

Nitori beamed a smile at him and took his food up to his bunk. As he walked away, Rin realized that he had hitched up his otherwise loose t-shirt and made a knot in it, leaving his stomach exposed in a very appealing way to Rin. His face heated up, his fists clenching and teeth gritting as he was having an even harder time controlling himself. When Nitori had climbed up and say on his bed, he noticed Rin’s eyes still on him. 

“What’s wrong, Rin-Senpai?” Rin jumped slightly, coming out of his daze and loosening his hardened expression.  
“Nothing, Ai.” Nitori cocked an eyebrow but said nothing. They ate in silence on separate beds, Nitori finishing first and climbing down to throw out his trash, knowing it would not get disposed of if he left it on his bed.  
“Do you plan on wearing that all day?” Rin spoke, Nitori turning to look at him. He looked frustrated, his food barely touched, his eyes just focused on Nitori’s slim waist; it was then he noticed exactly the effect he was having on his senpai.  
“I can take off the skirt if it really bothers you that much, Senpai.” Rin seemed to let out a breath and nodded.  
“Ai, what the hell?!” Rin exclaimed as he looked back up from his food. Ai had just slipped off the skirt right in the middle of the room, tossing it with some other clothes he had in a small pile. He’d put it away later, he just didn’t want Rin to know where he kept his girly clothes.  
“What?” He questioned back.  
“You couldn’t change in the bathroom or something?” He tried to get his voice level again.  
“But, Rin-Senpai, I change with you in the room all the time.”  
“Y-Yeah, but not while you’re wearing that.” His voice almost trailed off and Nitri had to strain to hear him. He looked down at himself, noticing that it was rather obscene the way his cock almost jutted out of the underwear, stretching the front slightly… and he wasn’t even erect yet.  
“Are you flustered, Senpai?” Ai asked outright, flirtily and while looking right at Rin; he nearly choked on his food for the second time that day.  
“Honestly, yeah, a bit.”  
“How come?” Nitori pressed, moving closer to Rin and smirking. Rin blushed slightly, catching the look before placing his food on the table next to his bed and scowling.  
“You know perfectly well ‘how come’.”  
“If I’d have known you’d pay this much attention to me, I’d have worn this months ago.” He kneeled on Rin’s bed, his hands going on Rin’s shoulders. As oblivious as Ai could be, he knew there was no way he was misinterpreting the situation.  
“Ai…” Rin warned, trying to look away but his gaze kept getting caught on Nitori’s waist.  
“What is it, senpai? Aren’t you gonna finish your dinner?” He asked innocently, his arms now wrapping around Rin’s neck as he moved in closer, still kneeling as if presenting his chest to Rin as a gift. Rin growled lowly, his hands gripping Nitori’s waist possessively before he pushed him back on bed.  
“I’m hungry for something else.” He spit back quickly before latching his teeth onto Nitori’s neck. 

It was more pleasurable than painful seeing as he didn’t draw blood. Rin’s tongue was quick to soothe the bitten spot, his hands trailing up and down Nitori’s arched sides. The room quickly filled with little pants and whimpers from Ai as Rin trailed around to the other side of his neck. He began to pepper small kisses along his jawline, a leg coming in between Nitori’s as he ground down into him. His lips were mere millimeters away from Nitori’s before he slowed to a stop.

“Is this okay?” He asked Nitori who nodded viciously.  
“Please, kiss me, Senpai.” He spoke softly and Rin’s heart felt heavy with the words.

He swooped down, catching the smaller boy’s lips with his own, his body absentmindedly continuing his previous motions. Nitori took Rin’s face in his hands, holding on tightly as if afraid that he was dreaming. He kissed back with fervor and passion, thrusting up against his senpai’s leg. Rin bit on his lip softly as Nitori tugged his hair, Rin’s tongue licking over his bottom lip and deepening the kiss. As Nitori continued to pant and breathe heavily, Rin’s hand made its way down to his underwear, cupping the growing bulge against the soft material. Nitori began to whine and whimper. 

“P-Please, Rin-Senpai…” He spoke, not knowing what else to say.  
“What do you want, Ai?” Rin asked, his breath warm on Nitori’s ear as he licked a stripe across the shell of it.  
“Ngghhh…”

Nitori grabbed the tank Rin was wearing and tossed it to the side; neither of them could care much where it went in their heated fumbling. Rin leaned back to take off his sweatpants but Nitori’s hand grabbed his wrist, stopping him as lithe fingers trailed across his stomach, taking pleasure in every dip of his well-defined abs. Rin watched as Nitori’s eyes shone with wonder and need, feeling the fingers soon dip lower and grab the waistband of his pants to help him pull them off. Rin quickly jumped back into action and disposed of his pants, tossing them aside as he licked a stripe up Nitori’s stomach. He undid the knot of the shirt, his mouth somewhere along his ribcage and tacitly told Nitori to lift up as he removed his shirt. 

Rin’s cold finger passed over a warm and hardening nub and he twisted it around in his fingers, finding delight as Nitori arched again, writhing against the sheets and balling them up in his fists. Rin slowly brought his mouth to the other nipple, teasing it slowly with his tongue as Nitori’s hands moved to tug at his hair instead. He groaned against the younger boy’s chest and began rutting against him again. He pulled back with a kiss that was much too short for Ai’s tastes. He kneeled, looking down at the younger boy’s small, almost naked body. His hands ran down to tease the growing bulge in his feminine underwear, watching as Nitori clamped his eyes shut and ground up against his senpai’s hands. Rin couldn’t resist bending down to suck on the bulge over the warm cotton and found hands in his hair almost immediately. He pressed his tongue against the cotton as his fingertips teased and snapped the bands of the thigh-highs. When Nitori opened his eyes and looked down he was met with Rin’s unwavering gaze. He almost squeaked and threw his head back down on the mattress. Rin led kisses up his body, pressing a small kiss to the bulge he was sucking on and trailing kisses along his hipbones, stomach, chest, until he reached Ai’s mouth. He had to take his hand away from it, allowing Ai to moan into his mouth as his hand slipped underneath the shielding fabric of his underwear to grab Nitori’s erection. 

Rin was quickly met with thrusts from Nitori’s hips, his cock starting to leak in the older boy’s hands. Rin licked at his neck before moving down again in one swift motion, taking the underwear and pulling them off, smirking as he saw the wet spot on them before filling his mouth with Nitori. Nitori’s hand didn’t make it to his mouth in time and let out a high-pitched, strangled moan before it was cut off quickly. Rin continued his sucking, allowing his thumbs to rub little circles into Ai’s hipbones, trying to calm him down. He looked up after a moment, and knit his eyebrows together when he noticed that Nitori was biting his hand. The pressure on Ai’s cock let up and Rin was soon there to kiss him.

“You’ll hurt yourself like that.” Rin said softly against his lips, rubbing his thumb over the indented area on the back of Ai’s hand.  
“I-I’m sorry, Senpai. I can’t help it.” His face was a blushing, writhing, darkened mess. 

Rin kissed him at hearing those words; that boy was too cute for his own good. He slipped off Nitori’s underwear, his fingers lightly teasing the fabric of the socks in the process. As much as it bothered him, he still had to pull away, getting up to go fetch a bottle of lubricant from his desk. He rid himself of his boxers in the process and noticed Nitori’s eyes lingering on him. He observed the boy’s form for a moment as the same was done to him before he reached over and picked up a black fabric that had been thrown across the room much earlier. Nitori’s eyes went wide as Rin came back with the item in his hand. 

“I want you to put it back on,” He spoke, shoving it into Nitori’s hand while kissing his neck again. “Can you do that for me?” His words were soft and warm in Ai’s ears. The gray-haired boy nodded and slipped on the fabric, much to Rin’s excitement. “You look so good like this, Ai. Can’t believe you waited this long to let me see you like this.”

Nitori began to whimper again as Rin’s hand was wrapped around his red and swollen cock. He watched as Rin grabbed the bottle and used both hands to spread some lube on his fingers, leaving his skirt tented with his erection. As Rin pushed his hips up, he watched the skirt fold and fall across his stomach, able to see now as Rin pushed in one finger and the other wrapped around his dick. He pushed back on the finger, knowing he could take more while Rin’s hand left his erection to stabilize himself as he moved up to kiss Nitori again. 

“A-Another…” He whispered softly into the ear of the red-haired boy who was now kissing his neck. He thought the process in his entrance was developing much too slowly.  
“Are you sure?” Rin asked and while Nitori found the concern cute and heart-warming, he would much rather want something else inside of him.  
“Y-Yes. I can take it.” He reached his hand down to grab two more of Rin’s fingers and pressed them against his entrance.  
“A-Ai! That’s too much-” He was cut off by a moan as Ai pressed back against his hand and was buried to the first knuckle with three fingers inside of him. Rin marveled at the sight.  
“I-Isn’t my first time d-doing this, Senpai.” Nitori mustered back as he continued to push after noticing Rin’s questioning glance.  
“Fuck…” Rin muttered, leaning his head against Nitori’s chest as the image of Nitori fingering himself came to mind.  
“P-Please, Senpai, I’m ready. Don’t tease me anymore.” Rin tugged on his lip softly before pulling his fingers out. 

He lubed himself up sufficiently, not wanting to hurt Nitori. Ai watched the sight before him as he stroked himself. Rin swatted his hand away, taking it in his own instead as his other hand was helping him line up with Nitori’s entrance. The younger boy’s chest was rising and falling rapidly: he couldn’t believe this was happening. Rin was pressing in slowly and Ai was too anxious for this to happen already. He leaned himself up on his arms and shifted himself into Rin’s lap. Rin, being mindful of Nitori, kept his body tilted so he wouldn’t press into him so quickly; he obviously wasn’t getting the message. 

“S-Sen-”  
“C-Call, me Rin, Ai. Just Rin.” He said, cutting him off and wrapping his arms around the boy’s waist.  
“Fuck me, Rin.” Nitori whispered in his ear and curved his body inward, taking the rest of Rin to the hilt as the latter groaned loudly into the room both at the sound and feel of Nitori. 

Ai began to move slowly on Rin’s lap, using his hands to brace himself on Rin’s shoulders. Rin’s fingertips began to dig bruises into Nitori’s hips. He had initially tried to get the boy to slow down but eventually just went with the quicker rhythm Ai had set and thrust up into the boy, losing himself inside Nitori’s hot and tight interior. 

“F-Faster, Rin. P-please… harder… fuck me harder...” The expletive certainly did the trick as Rin grabbed his waist and pounded into him. There would definitely be marks in the morning, especially now that Rin was biting into his neck again.  
“Such a filthy mouth, Ai. Keep talking for me.” He breathed hotly, one hand moving to trace the delicate curve in his back.  
“I-I’ve been wanting this for so long, Rin. Just wanted to ride your big cock until I came. I touched myself thinking about you Rin. Fingered myself and wished it was you instead.”  
“Fucking hell…” Rin cursed, leaning his head against the younger boy’s shoulder, which may have been a bad idea considering now he just had a view of the skirt with Nitori’s cock jutting out and pushing the front fabric into the dip between his stomach and raging erection. Or maybe that was a good idea. He noticed Nitori’s hand on it and made his own join it.  
“Se-- Rin, please… I’m so close.” Rin was too, his fingers wrapping around Nitori’s as they moved on his cock in unison. 

He felt the heat clamping around him with every stroke until it became impossibly tight and he felt a warm liquid trailing over his hand, soiling his skirt. He kissed Nitori through his orgasm, bringing him back down. The boy barely took a breather before pushing Rin down, supporting himself on his legs and Rin’s chest with his hands, and practically bouncing on his dick. His hole was oversensitive but he gave himself over to Rin anyways, going faster with each thrust as Rin grunted and chased his breath. 

“Cum in me, Rin.” He looked down at his senpai and that did it for Rin. He rode out his climax, watching all of Nitori at the moment. His contorted yet pleasured face as he dug his fingertips into Rin’s chest, The black thigh-highs which perfectly cupped his legs and led to his soiled skirt which barely hid his cock, and the blush that spread itself down his face, ending at his open and moaning mouth. 

He felt his cock go slightly colder and the mattress shift as Nitori dismounted and lay on next to him. He took off the thigh-highs and tossed them somewhere. He then took off his skirt and stared at it, knowing it could not be saved. It was his favorite but he shrugged, knowing the occasion was worth it and, maybe if he scrubbed hard enough he could get the stains out. He tossed it to the side along with the socks, grabbing a few napkins to clean both of them up, wiping away stray drops of his own seed that had landed on Rin’s chest. He jumped as he leaned over to throw away the napkin and was met with Rin’s arms around his. He came down next to his side and received a kiss on the top of his head.

“So cute, Ai…” He trailed off, growing sleepy. Rin let him go briefly so he could stand to turn off the light but kept his arms outstretched for when Nitori returned. Nitori smiled and allowed himself to be wrapped in one of Rin’s arms as he tossed the blanket over them.  
“R-Rin?” He inquired after a few moments. Rin’s eyes slowly shuttered open.  
“Hmm?” He asked softly. Nitori blushed and suddenly Rin was more alert. “What is it, Ai? You know you can tell me anything.”  
“A-Are we… does this mean… Can I be your boyfriend?” He hid his face, not wishing to see Rin’s reaction. But Rin used a hand to lift his face up by his chin, meeting Nitori’s sad eyes with a smile and then a kiss.  
“Of course, Ai. I’m surprised it took you this long to realize.”  
“Realize what?”  
“That I like you.” Nitori’s eyes went wide.  
“Wh-What? You liked me before today?”  
“Of course, Ai!” He exclaimed without really raising his voice.  
“I always thought I was more obvious.”  
“Honestly, I just thought you were like that with everyone.”  
“No… just you, Senpai.”  
“Rin.” He corrected with a smile.  
“Rin,” Nitori repeated. “So if you’ve liked me for so long, why did you act on it today?”  
“I couldn’t help myself. You prance around in that cute little skirt and those thigh highs and you expect me not to pounce on you?” He chuckled and Nitori blushed before settling into the crook of Rin’s neck and smiling.  
“I guess I have to show you the rest of my collection then.” He said softly and Rin smirked, blushing slightly and holding his boyfriend in his arms. He definitely couldn’t wait to wake up and make Nitori try on a new outfit.

**Author's Note:**

> Kudos, comments, concerns, questions, etc. are all appreciated ^-^ Thanks for reading!


End file.
